Diethyl Ether → HCID 20737861, compound

Participants

Reaction Steps

A mixture of the above (S)-3-(1-tert-butoxycarbonyl-2-pyrrolidinyl)methoxyphenyl acetic acid in CH2Cl2 (10 mL) and TFA (10 mL) was stirred for 1 hr at room temp. Et2O was added to the mixture and allowed to stand. Upper layer was removed by decantation to give an oil. A mixture of this oil in water (100 mL), dioxane (30 mL) and NaHCO3 (6.0 g) was added Fmoc-Cl (2.86 g, 11.1 mmol) and the mixture was stirred for 20 hr at room temp. The mixture was extracted with Et2O (×2), and the aqueous layer was acidified by the addition of 1 N HCl. The mixture was extracted with EtOAc. The extract was washed with water, brine, dried over MgSO4 and concentrated in vacuo to afford 5.08 g (81%) (S)-3-(1-Fmoc-2-pyrrolidinyl)methoxyphenylacetic acid as a viscous oil.

Provenance & Evidence